Henry certainly ticks the first box, remaining Arsenal's record goalscorer and having been a vital part of the 'Invincibles', as well as winning a multitude of trophies at Barcelona.
Whether or not the Frenchman can repeat his achievements from the touchline remains to be seen.
'Zizou' was one of the greatest players of his era, and scored one of the most memorable goals in Champions League history to win the final for Real Madrid in 2002.
His success in the competition continued as a manager, becoming the only coach to ever win the Champions League three times in a row in his three seasons at the helm of Los Blancos.
Perhaps the most impressive example in recent history. Guardiola was an influential midfielder for Barcelona in the 1990s, winning multiple titles and one Champions League.
He managed the Barca B side before stepping into the hot-seat at Camp Nou and the senior squad won everything under his leadership. He then broke domestic records in Bundesliga and the Premier League with Bayern Munich and Manchester City en route to league titles with both clubs.
As a coach, Ancelotti has been even more impressive, with title wins in four different countries and three Champions League successes, including Real Madrid's long-awaited Decima. He is now at Napoli, having taken over from Maurizio Sarri in the summer.
A rare case of winning titles with both Real Madrid and Barcelona as a player, including three league titles and the Cup Winners' Cup.
He had an incredibly successful three-year spell in the Camp Nou dugout and has recently taken charge of the Spain national team.
A two-time Serie A and Cup Winners' Cup winner with Sampdoria and Lazio as a player before enjoying his most notable success as a manager with Inter - three league titles in his first stint - and overseeing Manchester City's first ever Premier League title in dramatic fashion.
He has since had a less successful return to Inter in-between spells at Galatasaray and Zenit St. Petersburg and is now managing the Italy national team.
As a player with AC Milan, the Italian won Serie A twice, the European Cup twice and numerous other cup competitions during the 1960s.
Widely regarded as one of the best players to ever grace a football field, Beckenbauer was instrumental to Bayern Munich's dominance in Germany and Europe during the 1970s as well as winning the World Cup for his country.
As a manager, he won the World Cup again - becoming just the second man of three to lift the trophy both as a player and coach - and picked up league titles with Bayern Munich and Marseille.
Cruyff won eight league titles and three European Cups with Ajax before claiming La Liga with Barcelona as a player.
He then returned to Camp Nou as a manager and won 10 titles, including four Liga titles and the European Cup, and is cited as the inspiration behind the successes of Guardiola, Jose Mourinho and a host of other modern managers.
As a player, the German won the Bundesliga and UEFA Cup with Borussia Monchengladbach as well as the World Cup and European Championships before tasting considerable success with Bayern Munich as a manager, including the treble in 2012-13.
Last season he returned to steady the ship at Bayern following the sacking of Carlo Ancelotti and led his side to the Bundesliga title once more.
A hero among Celtic fans as a player in the 1970s before similar success at Liverpool heading into the 1980s.
He is the last Liverpool manager to win the league title in England and oversaw Blackburn Rovers's sole Premier League title win in 1994-95 before a spell at Newcastle and a short stint at Celtic. He returned to Liverpool in 2011 after a decade out of the game, but lasted just 16 months.
Considered one of the best goalkeepers in the history of the game, he won a multitude of titles with Juventus and tasted international success in the World Cup and the European Championships with Italy.
As a manager, he won the double with the Bianconeri in the 1989-90 season, but was less successful with Lazio and the national side.
He also took charge of Real Madrid twice, winning La Liga both times. His management of the England national team proved far less fruitful, however, and he went on to coach the Russian national side and Chinese Super League club Jiangsu Suning before announcing his retirement at the end of last season.
'El Cholo' has forged an excellent reputation for himself back in Madrid as a manager, leading Atletico to a shock La Liga triumph in the 2013-14 season, winning the Europa League twice, and reaching two Champions League finals.
He played for some of the best teams in France and Argentina as a player but came into his own as a manager, particularly with Boca Juniors where he won four league titles and the Copa Libertadores three times.